Classifications

• • C—CHEMISTRY; METALLURGY
  • C03—GLASS; MINERAL OR SLAG WOOL
  • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
  • C03C27/00—Joining pieces of glass to pieces of other inorganic material; Joining glass to glass other than by fusing
  • C03C27/04—Joining glass to metal by means of an interlayer
  • C03C27/048—Joining glass to metal by means of an interlayer consisting of an adhesive specially adapted for that purpose
• • C—CHEMISTRY; METALLURGY
  • C03—GLASS; MINERAL OR SLAG WOOL
  • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
  • C03C27/00—Joining pieces of glass to pieces of other inorganic material; Joining glass to glass other than by fusing
• • C—CHEMISTRY; METALLURGY
  • C03—GLASS; MINERAL OR SLAG WOOL
  • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
  • C03C27/00—Joining pieces of glass to pieces of other inorganic material; Joining glass to glass other than by fusing
  • C03C27/06—Joining glass to glass by processes other than fusing
  • C03C27/10—Joining glass to glass by processes other than fusing with the aid of adhesive specially adapted for that purpose
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
  • C09J5/02—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving pretreatment of the surfaces to be joined
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J2400/00—Presence of inorganic and organic materials
  • C09J2400/10—Presence of inorganic materials
  • C09J2400/14—Glass
  • C09J2400/146—Glass in the pretreated surface to be joined
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
  • Y10T428/00—Stock material or miscellaneous articles
  • Y10T428/31504—Composite [nonstructural laminate]
  • Y10T428/31652—Of asbestos
  • Y10T428/31663—As siloxane, silicone or silane

Definitions

• the invention relates to a primer which is used for the pretreatment of glass surfaces which are to be bonded to rigid or flexible substrates by means of conventional adhesives.
• Another object of the invention relates to the use of the glass primer.
• the primers according to the invention contain organosilazanes as a characteristic constituent.
• Organosilazanes are reaction products of organohalosilanes with ammonia or amines. In the case of the present invention, the reaction products with ammonia are preferred. Products of this type are not new; their manufacture is described, for example, in German Offenlegungsschrift 28 34 027. Because of their Si-N bonds, organosilazanes are inherently substances sensitive to hydrolysis. It is also known that these products have been used as mold release agents in the rubber industry. It is all the more surprising for a person skilled in the art that organosilazanes can improve the resistance to hydrolysis of glass bonds, in particular also the resistance to hydrolysis of bonds between glass and elastomers.
• the organosilazanes used according to the invention can be prepared by the process of German Offenlegungsschrift 28 34 027. Then you go from Solutions of the corresponding organohalosilanes in inert solvents and under pressure and at temperatures between 0 and 50 C with liquid ammonia.
• Suitable organohalosilanes which can be further processed by this process to give the organosilazanes used according to the invention are diorganodihalosilanes and / or organotrihalosilanes or triorganohalosilanes.
• the chlorine compounds are preferably used as the starting point. However, the bromine compounds can also be used as starting materials.
• organosilazanes thus produced and used according to the invention contain organic groups which are bonded directly to silicon. These organic groups can be alkyl or aryl groups. Organosilazanes which have the same or different carbon residues on the silicon can be used according to the invention.
• Suitable Si-containing aromatic radicals are phenyl groups or substituted phenyl groups, suitable aliphatic radicals preferably have 1 to 7 C atoms, so methyl, ethyl, propyl, isopropyl, butyl, pentyl, neopentyl, hexyl, Cyclohexyl or benzyl groups are bound to the silicon.
• the side groups can in turn have further functional groups, provided that such groups do not react with the Si-N bond. Suitable functional groups are, for example, amino or mercapto groups.
• Organosilazanes with olefinic double bonds for example vinyl or allyl groups, can also be prepared and used.
• Preferred organosilanzanes are the reaction products of methyltrichlorosilane and / or dimethyldichlorosilane with an excess of ammonia according to DOS 28 34 027 and the analogous propyl compounds.
• the glass primers according to the invention can furthermore contain polyfunctional isocyanates.
• the use of multifunctional isocyanates is not mandatory, but is recommended if, for example, glass is to be glued to metals.
• Suitable polyfunctional isocyanates are primarily diisocyanates, for example aromatic diisocyanates such as tolylene diisocyanate, xylylene diisocyanate, diphenylmethane diisocyanate or technical (more condensed) diphenylmethane diisocyanate (functionality around 2.3).
• Aliphatic diisocyanates such as isophorone diisocyanate are also suitable. Instead of the diisocyanates themselves, prepolymers can also be used.
• prepolymers from polyfunctional alcohols especially from diols and triols, such as ethylene glycol, propylene glycol, condensed ethylene and propylene glycols, glycerol, trimethylolethane, trimethylolpropane and / or pentaerythritol with a significant excess (more than 20 mol%) of the aforementioned aliphatic and / or aromatic diisocyanates suitable.
• prepolymers are used in many areas of technology and are well known to the person skilled in the art of adhesives. They can be obtained as such or prepared by mixing the raw materials in a suitable ratio, the addition of the hydroxy compound to the diisocyanate being the preferred production process.
• Adducts of diisocyanates with polyfunctional alcohols can also Adducts of the aforementioned aromatic or aliphatic diisocyanates with polyfunctional epoxides can be used.
• the reaction product of triglycidyl isocyanurate with diphenyl methane diisocyanate in a molar ratio of 1: 3 or the reaction product of diglycidyl ether of bisphenol A with diphenyl methane diisocyanate in a molar ratio of 1: 2 is a suitable additive.
• the glass primers according to the invention further contain a resin component.
• Preferred resins are phenolic resins, especially reactive phenolic resins.
• Reactive phenolic resins are understood to mean phenolic resins which are not yet fully crosslinked, ie which do not have a three-dimensional lattice-like molecular structure.
• Such reactive phenolic resins are, for example, acid-condensed phenol formaldehyde or resorcinol formaldehyde resins which are usually referred to as novolaks.
• base-condensed phenolic resins which also contain hydroxymethyl groups and are capable of polycondensation when heated are also suitable.
• Phenol resins in the narrow S inn resorcinol-formaldehyde resins or coumarone-indene resins can be used.
• modified resins such as terpene-modified phenolic resins or mixtures with hydrogenated resin resins can also be used.
• An overview of phenolic resins can be found in Houben-Weyl, Macromolecular Substances, Part 2 (Volume 14) Georg Tieme Verlag, Stuttgart, .1963, pages 197 ff.
• both novolaks and resol resins e.g. Mixtures of novolak and tertiary butyl, phenol, resol resin are used.
• phenolic resins which have a viscosity of 1000 to 5000 mPas at 25 ° C. and still have OH numbers of about 300 to 500.
• Such products are known based on phenol, cresols, tertiary butylphenol, amylphenol or resorcinol or bisphenol A.
• silanes to be used in the primers according to the invention are known compounds which are generally recommended by commercial manufacturers as so-called adhesion promoters.
• Products containing reactive groups are preferred according to the invention, such as vinyltriethoxysilane, vinyltrimethoxysilane, vinyltris ( ⁇ -meth-oxyethoxy) silane, ⁇ -methacryloxypropyltrimethoxysilane, ⁇ -methacryloxypropyl-tris (2-methoxyethoxy) -silane, ⁇ - Mercaptopropyl-trimethoxysilane, ⁇ -aminopropyltriethoxysilane or the adduct of acrylic acid with this compound.
• silanes are also suitable: ⁇ -chloropropyitrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, vinyltriacetoxysilane, ß (3,4-epoxycyclohexyl) ethyltrimethoxysilane and N-ß- (aminoethyl) -j'-aminopronyltrimethoxysilane or its methacrylate in methanolic solution.
• Particularly suitable solvents for the primers according to the invention are ketones, esters, aromatic hydrocarbons, aliphatic hydrocarbons and halogenated hydrocarbons.
• Particularly preferred solvents are methyl ethyl ketone, alcohol / ketone mixtures, methylene chloride and mixtures thereof with ethyl glycol acetate.
• the application of the primers according to the invention is simple.
• the solutions are made in the usual way, i.e. applied to cleaned glass surfaces using spray guns, brushes or squeegees.
• the solvent is then evaporated and the second substrate is glued on with a suitable adhesive.
• the glass primers according to the invention are particularly suitable when polar or non-polar elastomers are vulcanized onto glass under conventional vulcanization conditions using conventional vulcanization adhesives. Suitable vulcanization adhesives are described, for example, in German patent application 30 41 841.8. In addition, such bonds can also be carried out with other conventional vulcanization adhesives.
• the usefulness of the primers according to the invention is not linked to vulcanization adhesives.
• Favorable results are also obtained when glass with polyurethane adhesives is to be bonded to other substrates. This applies particularly to glass-metal bonds. It is preferred to add a polyurethane prepolymer to the primer.
• the primers are also useful if they are to be bonded using one- or two-component epoxy adhesives or with commercially available acrylate adhesives.
• the particular advantage lies in a further increase in the hydrolysis resistance of the composites.
• the primers have proven particularly useful for composites that are exposed to long-term weathering when temperatures fluctuate widely. So with the use of the Primer manufactured composites to meet the requirements of automotive engineering.
• an EPDM 4 profile was extruded onto the coated glass surfaces.
• the EPDM extrudate was then vulcanized in a hot air cabinet at 170 ° C. for 15 minutes.
• these primers with PU adhesives can be used for metal bonding.
• the mixtures listed in the table below were prepared and, as mentioned in Example 1, applied to clean glass surfaces. After the primer layer had dried, the parts were coated with a commercially available PU adhesive layers and glued to steel after drying. Curing took place in the press at 160 ° C. for 30 minutes.
• test specimens were torn in a tearing machine.
• the results of the adhesion tests are summarized in the table below. Furthermore, the test specimens were stored in boiling water and then torn apart.
• Polyacrylate adhesive Commercial 2-component "No-mix” - 2nd generation acrylate adhesive, e.g. Pattex ® No-mix.

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• Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Organic Chemistry (AREA)
• Geochemistry & Mineralogy (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Materials Engineering (AREA)
• Ceramic Engineering (AREA)
• Adhesives Or Adhesive Processes (AREA)
• Paints Or Removers (AREA)
• Surface Treatment Of Glass (AREA)
• Joining Of Glass To Other Materials (AREA)
• Silicon Polymers (AREA)

Applications Claiming Priority (2)

Publications (3)

Family

ID=6224790

Family Applications (1)

Country Status (7)

Cited By (1)

Families Citing this family (31)

Family Cites Families (10)

• 1984
  • 1984-01-12 DE DE19843400860 patent/DE3400860A1/de not_active Withdrawn
  • 1984-12-22 DE DE8484116174T patent/DE3463157D1/de not_active Expired
  • 1984-12-22 EP EP19840116174 patent/EP0150482B1/fr not_active Expired
• 1985
  • 1985-01-08 US US06/689,619 patent/US4670057A/en not_active Expired - Fee Related
  • 1985-01-10 BR BR8500097A patent/BR8500097A/pt not_active IP Right Cessation
  • 1985-01-11 ZA ZA85278A patent/ZA85278B/xx unknown
  • 1985-01-11 ES ES539488A patent/ES539488A0/es active Granted
  • 1985-01-12 JP JP392485A patent/JP2515277B2/ja not_active Expired - Lifetime
• 1987
  • 1987-02-06 US US07/012,101 patent/US4735830A/en not_active Expired - Fee Related

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